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226788 Verruculogen (NA 209A, TR 1) CAS: 12771-72-1

Specifications
References
CAS Number
12771-72-1
Grade
Highly Purified
MDL Number
MFCD00079645
Molecular Formula
C27H33N3O7
Molecular Weight
511.6
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
(5R,10S,10aR)-1,10,10a,14,14aS,15bS-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propen-1-yl)-5H,12H-3,4-dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione

Fumitremorgin-type alkaloid. Tremorgenic neurotoxic mycotoxin. Selective blocker of KCa1.1 (high-conductance Ca2+-activated K+; BK; maxi-K) channels. Decreases GABA levels in CNS. Increases spontaneous glutamate and aspartate release. At toxic doses, increases the number and decreases the affinity of DHP receptors in rat cortex. Cell cycle inhibitor at the M phase. Inhibits calmodulin and PKC activity. Has apoptotic effects on human T lymphocytes. Stimulates the growth of seedling roots of buckwheat.

Synonyms
NA 209A; TR 1, (5R,10S,10aR)-1,10,10a,14,14aS,15bS-hexahydro-10,10a-dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methyl-1-propen-1-yl)-5H,12H-3,4-dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione
CAS Number
12771-72-1
Source
Aspergillus fumigatus.
Molecular Weight
511.6
Molecular Formula
C27H33N3O7
Identity
Determined by 1H-NMR and MS.
Solubility
Soluble in DMSO, 100% ethanol, methanol or dichloromethane.
Purity
≥98% (HPLC)
Form
Supplied as a white to off-white solid.
Storage and Stability
May be stored at 4°C for short-term only. Long-term storage is recommended at -20°C. Stable for 6 months after receipt. Protect from light when in solution. For maximum recovery of product, centrifuge the original vial prior to removing the cap.
References
1. Tremorgenic toxin from Penicillium veruculosum: R.J. Cole, et al.; Appl. Microbiol. 24, 248 (1972). 2. The structure of verruculogen. A tremor producing epoxide from Penicillium erruculosum: J. Fayos, et al.; JACS 96, 6785 (1974). 3. Verruculogen: a new substance for decreasing of GABA levels in CNS: L. Hotujac, et al.; Pharmacol. 14, 297 (1976). 4. Actions of tremorgenic fungal toxins on neurotransmitter release: P.J. Norris, et al.; J. Neurochem. 34, 33 (1980). 5. Actions of a tremorgenic mycotoxin on amino acid transmitter release in vivo: D.W. Peterson, et al.; Biochem. Pharmacol. 31, 2807 (1982). 6. In vitro effects of tremorgenic mycotoxins: M.I. Selala, et al.; J. Nat. Prod. 54, 207 (1991). 7. Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels: H.H. Knaus, et al.; Biochemistry 33, 5819 (1994). 8. Behavioral and biochemical effects of the tremorgenic mycotoxin verruculogen: L. Intorre, et al.; Environ. Toxicol. Chem. 46, 119 (1994). 9. Novel mammalian cell cycle inhibitors, tryprostatins A, B and other diketopiperazines produced by Aspergillus fumigatus. II. Physico-chemical properties and structures: C.B. Cui, et al.; J. Antibiot. 49, 534 (1996). 10. Total synthesis of fumitremorgins and verruculogens: T. Hino & M. Nakagawa; Heterocycles 46, 673 (1997). 11. Modulation of calmodulin and protein kinase C activities by Penicillium mycotoxins: I. Pala, et al.; Int. J. Toxicol. 18, 91 (1999). 12. Genotoxicity assessment of five tremorgenic mycotoxins (fumitremorgen B, paxilline, penitrem A, verruculogen and verrucosidin) produced by molds isolated from fermented meats: M. Sabater-Vilar, et al.; J. Food Protect. 66, 2123 (2003). 13. Influence alkaloids from the marine-derived strain of the fungus Aspergillus fumigatus Fresen. on the growth of seedling roots of buckwheat (Fagopyrum esculentum Moench): M. Anisimov, et al.; Int. J. Res. Rev. Appl. Sci. 13, 326 (2012). 14. Aspergillus fumigatus toxins cause cytotoxic and apoptotic effects on human T lymphocytes (Jurkat cells): H. Malekinejad, et al.; World Mycotoxin 6, 65 (2013).
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